Quaternary ammonium compound



Patented June 4,1940

UNITED STATES PATENT OFFICE m qua-manner momma COMPOUND Henry Ali'redfluott and John Blackley, Manchester, England,

116mm Bose, assignors to Imperial Chemical Industries Limited, a corporation of Great Britain No Drawing. Application June 10, 1938, Serial No. 213,031. in Great i i-mm June 11, 193':

1 Claims. (01. 260-294) This invention relates to the manufacture of new quarternary ammonium compounds which are also mono-substituted derivatives of urea.

According to the invention we 5 new quarternary ammonium compounds bycausing a urea of the general formula \t-r-un-c -Nm whereinR and R stand for the same or different alkyl, cycloalkyl or aralkyl radicals, or the grouping i N.- RI

1 as a whole stands for theradlcal of a heterocyclic 20 secondary base, for example, piperidine, morpholine or tetrahydroquinoline, and Y stands for the 1 group or for an arylene group, to

interact with a reactive ester derived from a monohydric or polyhydric aliphatic or araliphatic 25 alcohol and an inorganic acid or anorganic sulphonic acid. Suitable esters are, for example, ethylene chlorohydrin, benzyl chloride, methyl chloride, dimethyl sulphate, and ethyl p-toluenesulphonate.

In carrying the invention into practical eflect the urea is heated with the reactiveester alone or in a suitable solvent or diluent, e. g. an alcohol.

The products obtained are compounds of the general formula 1 BRE'N-Y-NH-CO-NH:

l ke

where RR. and Y have the significance given above, and R" and Ac stand for the groups or 40 atoms which taken together form the reactive ester. These compounds are readily soluble in water. They are useful for textile treatment purposes.

weight. Example 1 obtain the said The invention is illustrated but not limited by 45 the following examples in which the parts areby reaction involved in making this new compound may be illustrated by the following equation: (CH:):=NC H NHCONHI+(OBfi)is0le (c oeN-mm-rmoonm 404GB! Example 2 (CHa)2=NCHzCHzNHCONHa+CHaI-v (CHahENCHzCHaNHCO H Example 3 15.5. parts of s-piperidylethylurea are dissolved in parts of ethanol and 12.5 parts of dimethylsulphate are added. A vigorous reaction occurs "with evolution of heat. When the reaction has subsided, the mixture is heated to 100 C. for hour. It is then cooled and acetone is added, whereupon an oil separates out. This is separated oil and well washed with dry acetone, whereupon it crystallises, forming a white solid. This is then recrystallised from a mixture of acetone and alcohol. There is thus obtained 3- piperidylethylurea methosulphate in the form of white crystals of M. P. 216 C. The reaction involved in making this new compound may be illustrated by the following equation:

solos. Example 4 mide in the form of white crystals, M. P. 226 C.

with decomposition.

Example 5 15 parts of fl-piperidylethylurea and 8 parts 01' ethylene chlorhydrin are heated together at 100 C. for 6 hours in a vessel provided with a reflux of benzyl chloride out. This is separated or! and is then allowed to.

stand in a closed vessel containing phosphorus pentoxide, The oil gradually crystallises. There is thus obtained p-ureidoethyl-p-hydroxyethylpiperidinium chloride in the form of white hy-' groscopic crystals. V a

. Example 6 i v 43 parts of dibutylaminoethylurea and 25 parts for 16 hours. The mixture is then-allowed to cool whereupon it crystallises. There isthus obtained fl-ureidoethyl dibutyl benzyl ammonium chloride in the form of colourless hygroscopic crystals which are readily soluble in water.

Example 7 2" parts of dibutylaminoethylurea and 20 parts.

of methyl iodide are heated together for 24 hours in a steam-jacketed vessel provided with a reflux condenser. The mixture is then cooled, water is added and the aqueous solution'so obtained is washed with ether. The ether layer is rejected and the aqueous solution is evaporated to dryness.

.There is thus obtained methyl p-ureidoethyl dibutyl ammonium iodide in the form of colourless hygroscopic crystals which are readily soluble in water. The reaction involved in making this new compound may be illustrated by the following equation: j (o HoFNcmomNHc 0 NH,+oH,I

(G|Hn)r=NCH1CH;N'HC ONH:

We claim. 1. A quatern formula:

R lRI! I \N-OH.1CH:NH0 0-NH: R c wherein the grouping as a whole stands for the radical of a secondary group consisting of heterocyclic secondary bases and secondary amines in which R and R represent radicals selected from the category consisting of alinvl radicals, cycloalkyl radicals, and aralkyl radicals, R"

stands for a radical selected from the group consisting of aliphatic radicals and aralkyl radicals,

and Ac represents an anion of an acid selected from the group consisting of inorganic acids and organic sulphonic acids.

2. A process for the manufacture o1v new quaternary ammonium compounds which comprises causing a urea of the general formula:

/N-CH.|CHr-NHC0NH| are heatedtogether at 100 C.

ry ammonium compound of the wherein the grouping ganic acids and organic sulphonic acids.

3. A quaternary ammonium compound of the formula: I a R In" III-C Hz-C Hr-NH-C O-NH: R Ac wherein R and R, each represent alinvl radicals, R" stands for a, radical selected from the group consisting of aliphatic radicals and aralkyl radicals, and Ac represents an anion of an acid selected from the group consisting of inorganic acids andorganic sulphonic acids.

4. A quaternary ammonium compound of the formula:

R on: v zr-om-oni-nn-oo-Nm 4 a R wherein R and R each represent alkyl radicals.

5. A quaternary ammonium compound of the iormulaz.

I NCHr-CH+NHCONH: R Ac wherein the grouping selected from the. group consisting of inorganic acids and organic sulphonic acids.

6.'Beta piperidylethylurea methosulphate which has the formula CH:

C|Hio=I TC Hz-C H:NH,C O-NHs 7. Trimethyl beta-ureidoethyl ammonium iodide which has the formula a oHoENcmomNHc ONH:

ALFRED PIGdo'rr. DOVNALD ROSE.

HENRY JOHN ester derived from an class consisting of ali- 

